Writing illustration: a hand holding up an edited manuscript page beside a quill and ink pot
A handbook by Julian Shapiro

Writing Well

How do you write a first draft?

Writing your first draft

This is page two of a guide to Writing Well.

Many find that writing their first draft requires far more discipline than rewriting their first draft. It's hard to sit yourself down, think through half-formed ideas, and not get distracted by easier things.

That's why I recommend writing a terrible first draft as quickly as you can. Your goal is to speedrun—to blast through the laziness and the blockers to just get garbage onto paper. This shortcuts you to the rewriting phase, which most people find far less painful. It's strange how well this works.

That's why, in my bad first draft, I use placeholders any time I'm stuck: when an idea requires more thought than I want to put in, I just write <to fill out> and move on. My goal is to generate and connect ideas. Not to explain everything, and certainly not to say things well. Save that for future drafts.

This also means I don't care about being original in my first draft. Start with imitation then iterate toward origination over time. It's the only way to be efficient and avoid getting stuck.

I talk more about the craft of writing in my podcast discussion with James Clear (Atomic Habits) and Mark Manson. It's a good listen.
When you write a first draft, you write it for yourself. When you rewrite it, you write it for everyone else.
—Stephen King

The first draft process

Here’s the process you'll explore:

  1. Choose an objective for your post.
  2. Identify the ideas needed to accomplish your objective.
  3. Write a messy braindump for each point. Lean into your curiosity.
If you don't have a hard time getting your ideas onto paper, skip this page and continue to the next: Rewriting.

1. Start with your objective

Choose an objective that focuses your thinking and makes your goal clear.

Here again are the objectives from the previous page:

  1. Open people’s eyes by proving the status quo wrong. Example.
  2. Share a solution to a tough problem. Example.
  3. Distill an overwhelming topic into something approachable. Example.
  4. Tell a suspenseful and emotional story that imparts a lesson. Example.
  5. Articulate something everyone’s thinking about but no one is saying. Cut through the noise.
  6. Identify key trends on a topic. Then use them to predict the future.
  7. Contribute original insights to a field through your research and experimentation.

An objective reveals what your article must accomplish to be successful. You then use your intro—from the last page—to fish for the ideas that are most interesting to explore. Your objective and your hooks help you generate ideas for your outline.

Two types of ideas comprise your outline. Writing your first draft is the art of generating both of them:

  • Supporting points — Which points are needed to make my argument?
  • Resulting points — What are the implications of my argument being true?

Supporting points set the stage for your argument. Resulting points explore what happens when your argument is true. Meaning, you convince readers then you open their eyes.

2. Outline your ideas

Supporting points typically come first and resulting points typically come last. But, there is no correct outline. Hundreds of paths lead to your objective.

Here’s an example outline for the objective of Challenging the status quo:

  1. State that the reader’s current view of the world is false.
    Supporting point
  2. Establish how so many people being wrong about this hurts our world.
    Supporting point
  3. Establish what’s required to get everyone to change their view.
    Supporting point
  4. Predict how the world would be different once the transition is complete.
    Resulting point
  5. Explore the exciting byproducts of the world being different.
    Resulting point

More objective outlines

Articulate something everyone’s thinking about but no one is saying.

  • State what everyone's thinking.
    Supporting point
  • Establish why no one is saying anything.
    Supporting point
  • Predict the future implications of people staying silent.
    Resulting point
  • Predict how the world would be different if we brought attention to this.
    Resulting point

Identify key trends on a topic. Use them to predict the future.

  • State current trends.
    Supporting point
  • Establish the history and causation of these trends.
    Supporting point
  • Predict how these trends will play out.
    Resulting point
  • Establish why we should care about these implications.
    Resulting point

Contribute original insights to a field through research and experimentation.

  • Share your original insights.
    Supporting point
  • Explain how they contribute to a field.
    Resulting point

Distill an overwhelmingly complex topic into something digestible.

  • State the benefits of understanding the complex topic.
    Supporting point
  • Establish your credibility for explaining the topic.
    Supporting point
  • Break down the topic into something digestible.
    Supporting point
  • Explain how readers can benefit from this new knowledge.
    Resulting point

Share a clever solution to a tough problem.

  • Establish why it's such a tough problem.
    Supporting point
  • State the benefits of your clever solution.
    Supporting point
  • Walk through your solution.
    Supporting point
  • Explain how users can implement your solution.
    Resulting point
  • Predict how the world would be different if more people implemented it.
    Resulting point

Tell a suspenseful and emotional story that imparts a lesson.

  • Hook the reader with half-told story.
    Supporting point
  • Narrate the story.
    Supporting point
  • Establish the lesson from the story.
    Resulting point
  • Explain why the reader should care.
    Resulting point

3. Fill the outline

Under each talking point in an outline, I start by writing partially-formed thoughts.

It’s more efficient to speedrun through a bad first draft and improve it later than to try starting from completion.

It’s normal if few ideas come to mind immediately. You’ll discover that the majority of your ideas arrive while writing—not before. You write in order to think.

Later, you'll discover the rest of your ideas by resting and reflecting on what you’ve written. The act of writing compels your brain to draw connections between ideas.

It can’t help itself.

In general, you'll find ideas bubbling up from these places:

  • Hooks — Answer the captivating questions raised in your intro.
  • Experience — Reflect on observations and anecdotes.
  • Research — Acquire knowledge.
  • Experiments — Run tests.
  • Brainstorming — Voice-record then transcribe your thoughts.
  • Mental models — Think critically.

A reminder that the last page of this guide has a downloadable cheatsheet that handily recaps everything you're about to learn.

People think you need to be inspired to write. No, you write in order to get inspired.
—Paul Jarvis

Filtering your ideas

As you're writing, how do you know which thoughts are most valuable? What separates good ideas from bad ones?

My approach is to focus on ideas that are interesting or surprising. These are the ingredients of novelty. Novelty is what keeps readers reading. They tend to be:

  • Counter-intuitive
  • Counter-narrative
  • Shock and awe
  • Elegant articulations

Interesting ideas

To uncover interesting ideas, continuously make yournext point whatever interests you most. Skip everything that bores you.

When something bores you, it probably bores your readers too. And if something entertains you, it probably entertains them too. You're a proxy for your die-hard readers.

That’s the irony of self-indulgent writing: writing for yourself is the quickest path to writing something others love.

The mistake writers make is believing expertise is required to write compelling nonfiction. Nope, it's the rabid desire to indulge your curiosity.

I just write what I want. I write what amuses me. It’s totally for myself. I never in my wildest dreams expected this popularity.
—J.K. Rowling

Surprising ideas

In addition to interesting talking points, you're also looking for surprising ideas.

Surprise is anything that contradicts what readers know or expect you to say. It makes them think, “Wow. That’s unexpected.”

You generate surprising talking points using essayist Paul Graham’s method: First, learn the basic knowledge of a topic. Then, if you can find new information that surprises your knowledgeable self, it’ll surprise laypeople too. You can also play detective: when you know enough about a topic to know what's not known about it, you can selectively resolve those gaps and share the discoveries.

Again, you are your audience's proxy. There's no need to guess what will surprise them. Hunt for something that surprises you, and others will be along for the ride.

When you get stuck

When ideas stop flowing, ask yourself:

  1. How can I make this point more convincing?
  2. What are the interesting implications of what I just said?

Repeatedly ask these two questions and keep moving in whichever direction interests you most.

Your outline should be specific enough to provide structure, but loose enough to not confine expansive thinking. Whenever you feel a tug pulling you away from your outline, indulge that curiosity. Pursue that adventure.

You can prune the bad stuff later.

Refer to my blog post on how to generate good ideas: Creativity Faucet.
I hated English in high school. But if they called it Thinking, then I wouldn't be as terrible of a writer as I am today.
—Quoc-Anh Vu

4. Conclusions

I'm not convinced conclusions are necessary. But I like placing them after my resulting points to prompt readers into action. Here's how.

First, share a poignant takeaway

Identify your article’s significance by re-reading it and asking, “What was this really about? What was I trying to say?”

Distill the answer into a single, punchy sentence. Make readers think, “Ahh, yes, that's why this article was profound.”

Next, provide next steps

Now that your wisdom has resonated with readers, ask yourself, What about the world can my readers better appreciate now that they've read my article?

Share where they can go next to continue the journey they started here.

For a writing guide such as this, I might conclude by sharing bloggers whose work I enjoy. Then I might urge you to reverse engineer their articles and study what makes them great. That's how you continue your learning.

5. Rewrite

Your first draft is a sacred place for generating ideas.

Because it's while writing that you discover your best insights.

You write in order to think.

When you've squeezed every last drop from your brain, it's time to rewrite those ideas into something wonderful.

Onward.

Summary

Here is our writing process:

  1. Choose an objective for your post.
  2. Identify the talking points needed to accomplish your objective.
  3. Write a messy braindump for each point. Lean into your curiosity.

While writing, keep these points in mind:

  1. Don’t feel constrained by your outline. Expect to discover most of your ideas throughout the writing process.
  2. Trust that what interests you is what interests your readers. If not, target an audience more like yourself.

Here's how those steps fit into our overall writing process:

  1. Choose a topic
  2. Write your intro, and use it to brainstorm talking points
  3. Get feedback on your intro
  4. Create an outline using your objective
  5. Explore talking points within your outline
  6. Rewrite for clarity, succinctness, and intrigue ← The next page covers this
  7. Cycle between rewriting, resting, and receiving feedback
  8. Copy edit for grammar, word choice, and style
Chapter four
Rewriting
On the next page, turn a braindump into gold.
Next page
Drawn portrait of Julian Shapiro

Who’s Julian Shapiro?

I spend thousands of hours deconstructing how things work. I compile my insights into free handbooks like the one you’re reading. Over a million people read them annually. Insights that don’t make it in are shared on X.

Outside of writing, I invest in startups through Julian Capital and Deep Checks. Previously, I coded the world’s most popular web animation engine, Velocity.js, and I founded Demand Curve, the largest educator in startup marketing.

Submit deck